Chester, Illinois is a small town located on the banks of the Mississippi River.  It was founded in 1816 as a port on the western frontier centered around a flour mill, castor oil production, and moving goods up and down the Mississippi River.  “Where Illinois began,” became Chester’s motto as the town is just downstream of the first capital of Illinois, Kaskaskia–now an island created by the River.  The first governor of Illinois, Shadrach Bond, is buried in Chester on a plot in Evergreen Cemetery known as the smallest state park in Illinois.

Chester is the county seat of Randolph County where flags on display next to the courthouse depict the historic governing bodies of the area. The French (fleur-de-lis flag) settled in the area in the late 1600’s and governed until the end of the French & Indian War in 1763 when the British took control.  The Union Jack flew over the area until the Revolutionary War when Colonel George Rogers Clark and his Long Knives captured Kaskaskia on July 4, 1778.  Thereafter, the area was part of the Illinois Country and the Commonwealth of Virginia.  The Illinois state flag and the United States flag also fly at the courthouse.

In late 1803, Meriwether Lewis and William Clark stopped to engage additional military volunteers (at least 11) for their Voyage of Discovery of the Louisiana Territory.  At least 5 of the men chosen were permanent members of the voyage of discovery and made the entire trip to the Pacific Ocean and back.

Chester is the home of comic and cartoon character Popeye the Sailorman.  The creator of Popeye, Elzie Segar, grew up in Chester.  The 1875 opera house where he worked is now a Popeye museum and shop.  Popeye’s first appearance was in the Thimble Theatre comic strip in 1929.  Sprinkled throughout Chester are granite statues depicting various characters from the Popeye comic strip and cartoon.  These statues are the result of yearly fundraising that began with the placement of a bronze Popeye statue next to the Chester Bridge, the only place to cross the Mississippi between St. Louis and Cape Girardeau, MO.